Brightening of fiber material by coating with 1, 3-diaryl- and 1, 3, 5-triaryl pyrazoline derivatives



8-197 SR a ouiiwn nuum FIP83U XR 5&131079 M 3331 mg s Umted statesratent ice C. for 2030 minutes and the fabric is treated at boiling3131079 temperature for 30 minutes, then rinsed and dried. The

BRIGEITENWG 9F FE3ER MATERIAL BY CQATIPIG a b f .th VETH AND 1 ,5 Yfabric thus treated Shows a strong I'lgH-tfiilll'hg 61 601'. W1 @HNEDERIVATIVEg t a neutral white shade and good tfastness to light.

Annemarie Wagner and Siegfried Petersen, both of The bl'ightener Usedabove is p p y quatemizing Leverkusen, Germany, assignors toFarbenfabrilren the 1-p-dimethyl-aminopropyl-amido-sulfonyl phenyl-3-Bayer Aktiengesellschait, Leverkusen, Germany, ap-chlorophenyl-py-razoline (described in copending U15. corpomfiml ofGermany patent application Ser. No. 642,356, now abandoned, filed p iFilled Y 1961 123625 February 26, 1957, and assigned to the sameassignee and Chums pnomy aliphcanou Germany 1960 in the continuationthereof, co-pending application Serial 6 Clmms' 11733'5) No. 194,999,filed May 15, 1962) with dimethyl sulfate The present invention relatesto brightening agents of in a hl r nl n S lution at 80-95" C. Theproduct the diand tri-arylpyrazoline series; more particularly it has amelting point of about 200 C. concerns dior triaryil pyrazolinecompounds containing Example 2 a quaternary ammonium group. 15

Especially suitable brightening agents are 1,3-diphenyland1,3,5-triphenylpyrazoline compounds which contain a quaternary ammoniumgroup bound to the phenyl radical in the l-position or in the 5-positiondirectly or via a bridge member, such as an alkylene group, an -O-alkylene mu 3 a lane or a for 20 minutes. It is then rinsed and dried. Themaalkyline group phgnyl i of the 1,3 di2pheny1 terial thus treated showsa strong neutral White effect. or 1,3,5-triphenylpyrazoline compoundsmay carry fur- Example 3 tal'liltzrlsu-bstituentsl,1 flor example alkylgroups, substituted Into 150 Ice of a bath containing 0005 g of (hp-triygroups a ogen l methyl ammonium 1 r0 1 amido sulfonyl henylt i q' of thePIQPOSed c0n 1pOunds possible 3 p chlorophenyl-pyii az ol ine)-methylsulfate, th ere are r o brighten 111 an outstanding manner fibrematerials of the introdu ed 5 0 of acetat fibr The bath 1o '1 mostvaried type such as those of wool, cellulose acetate, 116mm h i i j g 2:23 Polyamldes l polymerisates' The applica minutes then rinsed anddried The acetate fibres show tail'on of the brightening agents isperformed in conventiona strong bluish fluorescence manner. Thefollowing examples serve to illustrate the invenffiijiig: 222 g g; 22 2:ff;- tion without, however, limiting the scope, thereof. fouzwingcompognay e 1 6 0 e 5 g. of a p'olyamide fabric are introduced into 200cc. of a bath containing 0.01 g. of (l-p-trimethyl-ammoniumpropyl amidosulphonyl phenyl 3 p chlorophenylpyrazoline)-methyl sulfate. The bath isslowly heated to 95-98" C. and the fabric is treated at this temperatureExample 1 orn 0.005 g. of (l-p trimethyl ammonium propylarnidosulfonylphenyl 3 p chlorophenyl-pyrazoline)-methy1 0 N sulfate of theformula H.('; H.

CHgCHg C11 CHZCH C2115 are dissolved in 2.0 cc. of hot water and dilutedwith 180 cc. of cold water. 5 g. of a polyacrylonitrile fabric are Q-fi3)3 SOACHT CHr-CH;

introduced into this bath. The bath is heated to 98 phenyl substitutedby lower alkyl; and Z is an anion group;

Q wherein p, q and m are whole numbers within the range f 1 the sum of 1lus bein 1-2- and n i a whole N CH so on- O P P q g s 3); 4 3 numberwithin the range of 0-3.

2. A process according to claim 1 wherein the fluorescent compoundcorresponds to the formula We claim: 3. A process according to claim 1wherein the fluores- 1. A process for improving fibers which comprisescent compound corresponds to the formula applying thereto an aqueoussolution of a fluorescent compound of the general formula. N(CH3)3 Ar%N\ Q l i N Xl (W)p Z9 H2C OH3 H o-0H 2 X 4. A process according toclaim 1 wherein the fluorescent compound corresponds to the formulawherein X stands for a phenyl; X stands for a member 5. A processaccording to claim 1 wherein the fluoresselected from the groupconsisting of phenyl and hydrocent compound corresponds to the formulagen; W is a substituent of the phenyl ring having the 6. A processaccording to claim 1 wherein the fluoresformula cent compoundcorresponds to the formula R1 in which Y is a member selected from thegroup consist- H26 ing of oxygen, sulfonyl, and sulfonylamido; R and RReferences Cited in the file of this patent are lower alkyl groups; R isa member selected from the group consisting of lower alkyl, lower alkoxyalkyl, UNITED STATES PATENTS and henzyl; Ar is a member selected fromthe group con- 2,567,796 Ackerman Sept. 11, 1951 sisting of phenyl,phenyl substituted by halogen and 2,639,990 Kendall May 26, 1953

1. A PROCESS FOR IMPROVING FIBERS WHICH COMPRISES APPLYING THERETO ANAQUEOUS SOLUTION OF A FLUORESCENT COMPOUND OF THE GENERAL FORMULA